There are many ways to express your feelings to someone you like without being obvious or making them feel trapped.
In fact, it is often said the best way to flirt is to keep the person you are flirting with guessing and not so sure if you are flirting with them or not.
But how do you do this? By asking good questions that are not obvious.
In this article, we have crafted a list of deep questions to ask your crush in a way that seeks to better understand them and know if they are into you or not.
Questions to Ask Your Crush
1. What is the nicest thing someone can do for you right now?
2. How have you been spending your time lately?
3. What would you do if I called late in the night?
4. What are you grateful for in life?
5. How do you know if you love someone?
Next: 100+ Questions to Ask a Guy
6. What is the craziest thing you do for fun?
7. What is the biggest deal-breaker on your first date?
8. What do you think about double texting?
9. Which song would you dedicate to someone you love?
10. How do you ask someone you have a crush on to go out with you?
Next: 100+ Sweet Things to Say to Your Crush
11. How do you know when you are falling for someone?
12. What do you do when you realize someone is falling for you?
13. What is the most important thing in your life right now?
14. What is the one thing you are least concerned about these days?
15. What are your thoughts on casual dating?
16. How important is money when it comes to dating? Is money overrated in a relationship?
17. What will you be doing this weekend?
18. What is the best gift you’d wish to receive from someone?
19. Have you ever experienced unreciprocated love?
20. If someone you have a crush on is not noticing it, what do you do?
Next: 100+ Questions to Ask a Girl
21. What do you think about casual relationships?
22. What do you do when you have a crush on someone?
23. What do you do if someone you like doesn’t like you back?
24. What do you think is overrated about relationships?
25. What scares you the most when it comes to love life?
26. What makes you nervous sometimes?
27. What are your thoughts on soulmates? Does it exist in the real world?
28. What crazy activities do you find to be fun?
29. Where do you live? What do you think about your neighborhood?
30. Who is your celebrity crush? What do you like about them?
Next: 100+ Perfect First Date Questions
31. What is your idea for an ideal first date?
32. What qualities do you look for in a girl you’d like to date?
33. What are you scared of right now?
34. What do you look for in a guy you like?
35. If I confessed to having a crush on you, how will you feel?
36. What is your idea of a perfect guy?
37. How would you describe your perfect lady?
38. What are you thinking about right now?
39. How did you think of me when we first met? Has anything changed so far?
40. What song do you listen to when you feel emotional?
41. If you are to dedicate a song to someone you have a crush on, what song will it be?
42. What are some of the most embarrassing moments in your life?
43. What is your biggest regret when it comes to relationships?
44. If you were to watch one movie together with someone you have a crush on, which movie will it be?
45. What is your turn-off when it comes to dating and relationships?
46. What makes men irresistible?
47. What do you find irresistible when it comes to women?
48. How likely would you approve of a lady making the first move?
49. Would you rather be called sexy cute or street smart?
50. How would you love your boyfriend dressed?
Get to Know You Questions
What are some flirty questions to ask your crush while texting? Well, these cute questions will give you a headstart if you want to get to know him or her.
51. What do you think of pet name? Would you like one?
52. How would you love your girlfriend dressed for a date?
53. How would you describe a perfectly happy relationship?
54. What are your top three things to do on weekend?
55. Does your name have any specific meaning?
56. What is the sweetest name someone has ever called you?
57. What is the nicest thing I have ever said about you?
58. Do you have a look-alike?
59. What is the one thing your parents don’t know about you?
60. Have you ever shot your shot? What happened?
Next: 100+ Flirty Questions to Ask Your Crush to Get to Know Him
61. Who are you sometimes mistaken for?
62. What do you do when someone flirts with you?
63. What is the nicest thing someone did for you?
64. What will people be surprised to learn about you?
65. What is the last thing you will ever do for love?
66. What do you do when heartbroken?
67. What is your favorite restaurant?
68. How do you celebrate your birthdays?
69. Which behavior do you consider rude while other people don’t?
70. What are your thoughts on astrology and signs?
Next: 100+ Deep Questions to Ask Your Crush to Get to Know Her
71. What do you think about the no-strings-attached type of relationship?
72. What is the one thing you don’t mind spending on?
73. What is the craziest thing you have ever done to get someone’s attention?
74. What do you like that most people find strange?
75. What is your ideal apparel for a dinner date?
76. Would you rather be loved or love someone?
77. What is your definition of a gentleman?
78. What is your definition of a lady? How do I fare?
79. What is the craziest thing you have done in the name of love?
80. What do you do when nervous?
81. What is the sweetest thing someone has ever said about you?
82. What is the weirdest thing that you still enjoy?
83. What is the one rule you live by?
85. How would you define yourself?
86. How would you describe your last relationship?
87. What is the one thing you are proud of about yourself?
88. What are some of the things we have in common?
89. Who do you look up to for inspiration?
90. Where would you like to travel to before you die?
91. What is the one song you cannot get out of your mind?
92. What is the one thing you look forward to?
93. What is your take on sexual activities before marriage?
94. What is your take on p#rn? Immoral or just okay?
95. When last did you feel awe and what happened?
96. Do you have a weakness you’d love to change?
97. If asked to change one thing about your body, what will you change?
98. What book would you suggest everyone read?
99. What do you think about true love? Does it exist?
100. What does beauty mean to you?
Funny Questions to Ask Your Crush
Flirting is a game and such, the goal is to be more interesting and funny to someone you have a crush on. These smooth questions to ask your crush will guide you.
101. When last did you make out?
102. How much do you like sexting in your free time?
103. What are some of your wildest sexual fantasies?
104. Have you ever tried making out outside in the open?
105. Have you tried making out in the car?
106. Would you prefer it with lights on or with lights off?
107. Have you thought of ever having a threesome in your life?
108. What is the strangest place you have ever made out?
109. What is your opinion of quickies?
110. How likely are you to make out with someone within the first month of knowing each other?
111. What do you feel most confident about your body?
112. Which body part do you get complimented most often?
113. What is your take on masturbation?
114. Have you ever tried edible underwear? What is your opinion of us trying one?
115. When last did you try a lube? What was your experience with it?
116. What do you consider dirty when it comes to dating and relationships?
117. How long do you think should the ideal s#x last?
118. What color of underwear do you think I am wearing right now?
119. Are you okay with me being naughty with you?
120. What did you first think of me when we first met?
121. What do you do to remain this attractive?
122. How do I get to know you better?
123. How are you so good at [add anything they are very good at here]
124. What do you wear to bed every night, if anything at all?
125. What is your idea of a perfect date?
126. What would you consider between day vs. night dates?
127. What is your number one turn-on when dating someone?
128. What is your favorite feature of a guy or lady you would prefer to date?
129. What will your reaction be if I kissed you right here right now?
130. What is the best thing I have ever said to you since we met?
131. How about we go out for a day or two this weekend?
132. How likely will you make the first move if you really like the guy or lady and you are sure they like you as well?
133. Have you ever gone skinny dipping? How about we arrange for one soon?
134. What is your ideal way to ask someone out for a date?
135. You know you look amazing, right?
136. Do you work out sometimes? You look amazing.
137. What is the most romantic date you have ever been on? What makes it so special?
138. Looking forward to getting a boyfriend or girlfriend any soon?
139. What would you do if I say I like you?
140. What is love to you?
141. What do you look for in a guy or girl?
142. What do you think about a new relationship right now?
143. How often do you take fake sick days? How do you spend them?
144. What is your ideal pet? Do you have one?
145. What is the last thing you would expect from someone you love?
146. What is the last question you’d want to hear from someone you love?
147. What are some of the happiest moments in your life?
148. Would you choose money over love?
149. How comes a beautiful person like you is single?
150. How updated are you on current affairs?
Juicy Questions to Ask Your Crush
Are you looking for juicy random questions to ask your crush and melt his heart away? This is what you should be asking:
151. What do you find funny about me?
152. What is the most common compliment you receive every now and then?
153. What is your definition of a perfect man or woman to date?
154. How would you describe me in 3 words?
155. Your name, what does it mean?
156. What do you do to remain this good-looking?
157. Whom would you call beautiful or handsome in our locality?
158. What is your idea of dating, love, and relationships?
159. How about we go on trails or hikes this weekend?
160. What is your number one turn-off?
161. What is your number one turn-on?
162. What is the most romantic thing to ever happen to you?
163. How will you describe your perfect kiss?
164. What would you say if I asked for a kiss right now?
165. How will you take it if I make the first move?
166. How would you describe your best feature?
167. Wanna sneak out tonight?
168. Do you know how beautiful or handsome you are?
169. Do you like texting or calling?
170. If I asked to touch any part of your body, will you allow it?
There you have a complete list of deep questions to ask your boyfriend or girlfriend or someone you have a crush on. The list is optimized in such a way that it barely feels like you are flirting while asking them.
It is said the best way to flirt is by making the person you are flirting with not realize it right away.
How do you Play?
The best way to play the game is by asking one question at a time following the 21 questions game style.
The first player starts with their “best questions to ask your crush” and soon as they are done with their 21 questions, the second player gets their chance to ask their questions too.
The game can be played using cards. You can also play the ask and drink version, or any other creative style that is ideal for your situation.
Above all, the rules of the game are for all players to be polite to each other.
If you are not comfortable answering specific crush questions or if you feel the questions are embarrassing, feel free to pass and move to the next one.
Questions not to Ask Your Crush
The best method of flirting with someone is to ask questions.
The responses to these questions will allow you to know if the person is into you or not and if they are ready for your affection.
However, there are questions that might not be received well by the person you are flirting with and they fall into these categories:
Personal questions are those that try to dig deep into a person’s private life or lifestyle.
Your crush is likely to be a new person in your life or someone you have admired for a long time.
When you get a chance to shoot your shot, be polite.
Do not ask questions in a way to clarify what you already know about them.
It is too early for that and this is likely to put them off for good.
Unwelcome Follow-Up Questions
Be mindful with your follow-up questions.
They are meant to clarify something and not to drive the point home.
If your crush seems uneasy with a question at any given point in your conversation, move to the next one.
Questions About Their Past
As the saying goes, “let the past stay in the past where it belongs.”
Ask only what needs to be ask and let the past stay in the past.
These questions are meant to help you understand each other and that should be your goal.